Contribution of heterobifunctional ligands to transition metal-catalysed C--C coupling reactions

Authors: AGNES LABANDE, ERIC DEYDIER, ERIC MANOURY, JEAN-CLAUDE DARAN, CATHERINE AUDIN, RINALDO POLI

Abstract: In this account the authors' latest results in C-C coupling catalysis are reviewed. First, an efficient catalytic system for the Kumada-Tamao-Corriu coupling reaction based on NHC-phosphine (NHC = N-heterocyclic carbene) nickel complexes is presented. Then the use of palladium complexes of chiral ferrocenyl NHC-phosphines in the asymmetric Suzuki-Miyaura coupling reaction is reported. High catalytic activities and moderate enantioselectivities (ee up to 46%) were obtained. Chiral ferrocenyl phosphine-ethers were also tested in the asymmetric Suzuki-Miyaura reaction yielding good activities and moderate enantioselectivities (ee up to 37%). Finally, the original synthesis of a ferrocenyl rhodium(III) complex and its successful use as catalyst for a C-C coupling reaction via C-H activation of 2-phenylpyridine is presented.

Keywords: Chiral ferrocenyl ligands, NHC ligands, P, O ligands, palladium, Kumada-Tamao-Corriu reaction, Suzuki-Miyaura cross-coupling, asymmetric catalysis

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